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The Total Synthesis of cis ‐7,8‐Dihydroxy‐11,12‐dehydrocalamenene by Regio‐ and Diastereo‐selective Alkylation of Chiral η 6 ‐Arenetricarbonylchromium Complexes: An Unexpected Case of Nucleophilic Aromatic tele ‐Substitution with Methoxide as a Leaving Group
Author(s) -
Schmalz HansGünther,
Arnold Markus,
Hollander Jens,
Bats Jan W.
Publication year - 1994
Publication title -
angewandte chemie international edition in english
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 0570-0833
DOI - 10.1002/anie.199401091
Subject(s) - chemistry , reactivity (psychology) , alkylation , methoxide , nucleophilic substitution , total synthesis , nucleophile , stereochemistry , sodium methoxide , block (permutation group theory) , medicinal chemistry , organic chemistry , methanol , catalysis , medicine , alternative medicine , geometry , mathematics , pathology
With complete diastereoselectivity and no loss of absolute stereochemical information , the chiral synthetic building block 1 is converted into 2 , an advanced intermediate in the total synthesis of the antiinfective sesquiterpene 3 . The reactivity of arene‐Cr(CO) 3 complexes is crucial to the synthetic strategy. TMS = SiMe 3 .